Sustainable synthetic methods: domino construction of dihydropyridin-4-ones and beta-amino esters in aqueous ethanol.
Domino reactions were designed to allow the byproduct of an upstream reaction to be internally recycled to catalyze a downstream reaction in a one-pot tandem sequence. Nitroarene reduction by In(0) generates an amine and In (III) byproducts. Addition of aldehyde followed by Danishefsky's diene or silyl ketene acetal provides access to dihydropyridin-4-ones or beta-amino esters, respectively, in yields that are comparable or superior to the reported stepwise reactions.
Alaimo
Peter J
PJ
Department of Chemistry, Seattle University, Seattle, Washington 98122, USA. alaimop@seattleu.edu
O'Brien
Robert
R
Johnson
Adam W
AW
Slauson
Sarah R
SR
O'Brien
Jeannette M
JM
Tyson
Elizabeth L
EL
Marshall
Amanda-Lynn
AL
Ottinger
Colleen E
CE
Chacon
Jon G
JG
Wallace
Lorien
L
Paulino
Corey Y
CY
Connell
Sarah
S
D002384:Catalysis; D004095:Dihydropyridines / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D000431:Ethanol / Q000737:chemistry*; D055772:Green Chemistry Technology; D014867:Water / Q000737:chemistry*
D004095:Dihydropyridines; D004952:Esters; D014867:Water; D000431:Ethanol; C038806:1,4-dihydropyridine